Inspired by people like Bret Victor and Michael Fogus, I decided to put together a list of the best books and essays that I read this year. After sharing it with my colleagues at CDG, I thought I’d post it here as well. Enjoy!

Daniel Kahneman: Thinking, Fast and Slow

I actually started this in 2013, but didn’t finish Part 3 until this summer. It’s a bit of a slow read, but this book has probably influenced me more than anything else I’ve read in the past five years. It’s essential reading for anyone who wants to understand human behaviour and decision making; it will change how you think about Thinking.

The point this book drives home is that humans do not — and probably cannot — make decisions in a totally rational manner. I find this especially interesting given how contemporary Western culture prizes rational, logical thought. So much of our scientific knowledge is built on inductive reasoning, which is vulnerable to confirmation bias and the availability heuristic.

From all the evidence presented in this book, some people might conclude that human thinking is flawed. But there’s another way of looking at it: rational thought is just one tool in our toolbox, and other modes of thinking can also be useful and effective when used appropriately. In fact, it’s possible that intelligence requires these other modes of thought.

Thanks to my sister Sheila for suggesting that I read this.

Nigel Cross: Designerly Ways of Knowing (1982)

In this short essay — which also appears as the first chapter in a book of the same name — Nigel Cross considers the idea that design, as a discipline, constitutes a “third culture” between science and the humanities. Cross is talking about design in the broadest sense: “the conception and realisation of new things…the arts of planning, inventing, making and doing”. Drawing on empirical studies of design, he argues that there are “designerly ways of knowing, distinct from the more usually-recognised scientific and scholarly ways of knowing”:

A central feature of design activity…is its reliance on generating fairly quickly a satisfactory solution, rather than on any prolonged analysis of the problem. In Simon’s inelegant term, it is a process of ‘satisficing’ rather than optimising; producing any one of what might well be a large range of satisfactory solutions rather than attempting to generate the one hypothetically-optimum solution.

[…]

The designer is constrained to produce a practicable result within a specific time limit, whereas the scientist and scholar are both able, and often required, to suspend their judgements and decisions until more is known — ‘further research is needed’ is always a justifiable conclusion for them.

This essay came at a perfect time for me. In the past year, I’ve begun to feel the rationalistic approach of science is overvalued in our culture, and that perhaps it’s not the best way of approaching certain issues. I find it interesting to think that design might offer an alternative approach.

Horst Rittel and Melvin Webber: Dilemmas in a General Theory of Planning (1973)

Maybe the most important thing I discover this year, this is the paper that introduced the concept of a “wicked problem”. As opposed to the “tame” problems of science and math:

[Wicked problems] cannot be definitively described. Moreover, in a pluralistic society there is nothing like the undisputable public good; there is no objective definition of equity; …it makes no sense to talk about “optimal solutions”…unless severe qualifications are imposed first. Even worse, there are no “solutions” in the sense of definitive and objective answers.

This paper totally changed my thinking on what it takes to address the biggest problems of our time. It’s now clear to me that climate change is not something that can “solved” using the toolkit of science and engineering, and I think it’s dangerous for us to keep pretending otherwise.

The classical paradigm of science and engineering…is not applicable to the problems of open societal systems. In the world of planning and wicked problems…the aim is not to find the truth, but to improve some characteristics of the world where people live. Planners are liable for the consequences of the actions they generate; the effects can matter a great deal to those people that are touched by those actions.

Ursula M. Franklin: The Real World of Technology

This book reflects another theme for me this year: trying to think more critically about the role of technology in our lives. Ursula Franklin is an experimental physicist, a former member of the Science Council of Canada, and a noted pacifist. In this book, she argues for a broader view of technology and how it influences our culture:

Technology is more than the sum of its wheels, gears, and transmitters. It is a system that involves organization, procedures, symbols, new words, equations, and, most of all, a mindset. Technology changes the social and individual relationships between us and forces us to examine and redefine our notions of power and accountability.

Thanks to Frank Chimero for recommending this.

Edward De Bono: Six Thinking Hats

Six Thinking Hats describes De Bono’s method of using deliberate role playing to improve thinking, communication, and decision making — particularly in groups. An alternate title for this book could be “Getting Things Done with Humans”:

Perhaps the biggest obstacle to quick and effective thinking is the ego. … Thinking is used to attack and put down other people. Thinking is used to get your own way. Thinking is used to show others how clever you are.

[…]

Confrontational and adversarial thinking exacerbate the ego problem. Six Hats thinking removes it.

Like some of the other authors in this list, De Bono believes that design thinking offers an alternative to the rationalistic approach:

Western thinking is concerned with “what is,” which is determined by analysis, judgement and argument.

That is a fine and useful system. But there is another whole aspect of thinking that is concerned with “what can be,” which involves constructive thinking, creative thinking, and “designing a way forward.”

Thanks to Alan Kay for recommending this.

Other things I enjoyed this year:

• Conal Elliot - The C Language is Purely Functional
• Peter Bailis - Data Integrity and Problems of Scope
• Jon Purdy - Why Concatenative Programming Matters
• Eric Giannella - Morality and the Idea of Progress in Silicon Valley
• Ted Nelson - It All Went Wrong at Xerox PARC (video)
• Kathleen Pine and Max Liboiron - The Politics of Measurement and Action
• The Recurse Center User’s Manual - Social Rules
• Kurt Ralsek - The Crit
• Mike Monteiro - How Designers Destroyed the World (video)